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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:16:40 UTC

Update Date

2021-09-26 23:01:38 UTC

HMDB ID

HMDB0250274

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cirazoline

Description

Cirazoline belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Cirazoline is a very strong basic compound (based on its pKa). It is believed that this combination of properties could make cirazoline an effective vasoconstricting agent. Cirazoline has also been shown to decrease food intake in rats, purportedly through activation of α1 adrenoceptors in the paraventricular nucleus in the hypothalamus of the brain. Cirazoline is a full agonist at the α1A adrenergic receptor, a partial agonist at both the α1B and α1D adrenergic receptors, and a nonselective antagonist to the α2 adrenergic receptor. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cirazoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cirazoline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0250274
     RDKit          3D
Cirazoline
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.6347   -0.7601   -2.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -0.9932   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107   -0.9521   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -0.6787    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6915   -0.6276    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -0.8647    2.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674    0.5559    2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -0.4470   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1710   -0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865    0.0851   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    0.3393   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599    0.3285    0.8344 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    0.6150    1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    0.6509    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    0.6320   -1.0186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.4847   -2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.7880   -3.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6194   -1.2124   -1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784   -1.1364    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.7276    1.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -1.2486    2.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -1.2498    3.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.1760    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    1.1054    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0760    0.9593   -1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -0.7743   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.2106    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713    1.5861    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832   -0.2653   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288    1.5751    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    0.8009   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488   -0.2922   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  2  0
 16  1  1  0
  7  5  1  0
 15 11  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

  Mrv1572010191514032D          

 17 19  0  0  0  0            999 V2000
    0.2955    0.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8870   -0.2802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196    0.8757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245   -1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4390    0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0265    1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933   -0.7806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 12  1  0  0  0  0
  2 14  1  0  0  0  0
  2 15  1  0  0  0  0
  2 17  1  0  0  0  0
  3 14  2  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250274

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]N1CCN=C1COC1=CC=CC=C1C1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15)

> <INCHI_KEY>
YAORIDZYZDUZCM-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.284

> <EXACT_MASS>
216.126263143

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.206769025114745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
1.6674871943333336

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.258458048758246

> <JCHEM_POLAR_SURFACE_AREA>
33.62

> <JCHEM_REFRACTIVITY>
62.69810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cirazoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250274
     RDKit          3D
Cirazoline
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.6347   -0.7601   -2.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -0.9932   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107   -0.9521   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -0.6787    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6915   -0.6276    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -0.8647    2.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674    0.5559    2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -0.4470   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1710   -0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865    0.0851   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    0.3393   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599    0.3285    0.8344 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    0.6150    1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    0.6509    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    0.6320   -1.0186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.4847   -2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.7880   -3.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6194   -1.2124   -1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784   -1.1364    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.7276    1.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -1.2486    2.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -1.2498    3.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.1760    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    1.1054    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0760    0.9593   -1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -0.7743   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.2106    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713    1.5861    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832   -0.2653   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288    1.5751    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    0.8009   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488   -0.2922   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  2  0
 16  1  1  0
  7  5  1  0
 15 11  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 19-OCT-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-OCT-15         0                                  
HETATM    1  O   UNK     0       0.552   0.103   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      -3.522  -0.523   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      -2.277   1.635   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.219   1.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.989   2.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.449   2.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.219   0.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.885  -0.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.553  -0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.885  -2.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.553  -2.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.782  -0.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.219  -2.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.115   0.103   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.553   0.621   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.783   1.955   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -3.721  -1.457   0.000  0.00  0.00           H+0
CONECT    1    8   12                                                       
CONECT    2   14   15   17                                                  
CONECT    3   14   16                                                       
CONECT    4    5    6    7                                                  
CONECT    5    4    6                                                       
CONECT    6    4    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    1    7   10                                                  
CONECT    9    7   11                                                       
CONECT   10    8   13                                                       
CONECT   11    9   13                                                       
CONECT   12    1   14                                                       
CONECT   13   10   11                                                       
CONECT   14    2    3   12                                                  
CONECT   15    2   16                                                       
CONECT   16    3   15                                                       
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0250274
HETATM    1  C1  UNL     1      -2.635  -0.760  -2.638  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.607  -0.993  -1.690  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.311  -0.952  -0.345  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.041  -0.679   0.111  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.691  -0.628   1.550  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.670  -0.865   2.606  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.367   0.556   2.311  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.075  -0.447  -0.844  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.201  -0.171  -0.451  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.286   0.085  -1.291  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.502   0.339  -0.453  1.00  0.00           C  
HETATM   12  N1  UNL     1       2.560   0.329   0.834  1.00  0.00           N  
HETATM   13  C11 UNL     1       3.891   0.615   1.308  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.736   0.651   0.065  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.775   0.632  -1.019  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.357  -0.485  -2.199  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.848  -0.788  -3.699  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.619  -1.212  -1.981  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.078  -1.136   0.419  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.613  -0.728   1.781  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.674  -1.249   2.415  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.249  -1.250   3.580  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.723   1.176   2.933  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.150   1.105   1.765  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.076   0.959  -1.953  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.444  -0.774  -1.977  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.232  -0.211   1.977  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.871   1.586   1.805  1.00  0.00           H  
HETATM   29  H13 UNL     1       5.383  -0.265  -0.011  1.00  0.00           H  
HETATM   30  H14 UNL     1       5.329   1.575   0.042  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.972   0.801  -2.031  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.549  -0.292  -2.920  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4    4   19
CONECT    4    5    8
CONECT    5    6    7   20
CONECT    6    7   21   22
CONECT    7   23   24
CONECT    8    9   16   16
CONECT    9   10
CONECT   10   11   25   26
CONECT   11   12   12   15
CONECT   12   13
CONECT   13   14   27   28
CONECT   14   15   29   30
CONECT   15   31
CONECT   16   32
END

HMDB0250274
     RDKit          3D
Cirazoline
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.6347   -0.7601   -2.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -0.9932   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107   -0.9521   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -0.6787    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6915   -0.6276    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -0.8647    2.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674    0.5559    2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -0.4470   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1710   -0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865    0.0851   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    0.3393   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599    0.3285    0.8344 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    0.6150    1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    0.6509    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    0.6320   -1.0186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.4847   -2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.7880   -3.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6194   -1.2124   -1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784   -1.1364    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.7276    1.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -1.2486    2.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -1.2498    3.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.1760    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    1.1054    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0760    0.9593   -1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -0.7743   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.2106    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713    1.5861    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832   -0.2653   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288    1.5751    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    0.8009   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488   -0.2922   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  2  0
 16  1  1  0
  7  5  1  0
 15 11  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cirazoline monohydrochloride	MeSH
2-(2'-Cyclopropylphenoxymethyl)imidazoline hydrochloride	MeSH

Chemical Formula

C₁₃H₁₆N₂O

Average Molecular Weight

216.284

Monoisotopic Molecular Weight

216.126263143

IUPAC Name

2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole

Traditional Name

cirazoline

CAS Registry Number

Not Available

SMILES

[H]N1CCN=C1COC1=CC=CC=C1C1CC1

InChI Identifier

InChI=1S/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15)

InChI Key

YAORIDZYZDUZCM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Imidolactam
2-imidazoline
Amidine
Carboxylic acid amidine
Ether
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250274)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.62	ALOGPS
logP	1.67	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.7 m³·mol⁻¹	ChemAxon
Polarizability	24.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.391	30932474
DeepCCS	[M-H]-	144.995	30932474
DeepCCS	[M-2H]-	179.399	30932474
DeepCCS	[M+Na]+	153.782	30932474
AllCCS	[M+H]+	149.9	32859911
AllCCS	[M+H-H2O]+	145.8	32859911
AllCCS	[M+NH4]+	153.7	32859911
AllCCS	[M+Na]+	154.8	32859911
AllCCS	[M-H]-	154.5	32859911
AllCCS	[M+Na-2H]-	154.4	32859911
AllCCS	[M+HCOO]-	154.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cirazoline	[H]N1CCN=C1COC1=CC=CC=C1C1CC1	2525.9	Standard polar	33892256
Cirazoline	[H]N1CCN=C1COC1=CC=CC=C1C1CC1	1808.2	Standard non polar	33892256
Cirazoline	[H]N1CCN=C1COC1=CC=CC=C1C1CC1	1926.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cirazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	2137.4	Semi standard non polar	33892256
Cirazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	2062.9	Standard non polar	33892256
Cirazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	2979.1	Standard polar	33892256
Cirazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	2370.3	Semi standard non polar	33892256
Cirazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	2286.5	Standard non polar	33892256
Cirazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1COC1=CC=CC=C1C1CC1	3095.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cirazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-148a4a388c57867edbac	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirazoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 10V, Positive-QTOF	splash10-014i-2290000000-9f267eef7a8a7b276ec8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 20V, Positive-QTOF	splash10-015i-9740000000-c4425a6ce8299104881b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 40V, Positive-QTOF	splash10-00kf-9200000000-d49282798f0c8c3acc6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 10V, Negative-QTOF	splash10-014i-1390000000-dc2d4187a3e3b85f16dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 20V, Negative-QTOF	splash10-001i-1910000000-223408d04c9af85841e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 40V, Negative-QTOF	splash10-000x-5900000000-8bb6381caa9b64976d82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 10V, Positive-QTOF	splash10-014i-0090000000-b3b3217a7e594f652193	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 20V, Positive-QTOF	splash10-014i-1490000000-c5b3c0118bf9f07eed0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 40V, Positive-QTOF	splash10-0le9-9100000000-cd98b2b369af30b6126e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 10V, Negative-QTOF	splash10-0159-0690000000-abb96aa4f9876fd7bf9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 20V, Negative-QTOF	splash10-001i-0900000000-4308f0a3986ad91b3e24	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirazoline 40V, Negative-QTOF	splash10-001i-4900000000-fbe6ad38b1ee708e7be6	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09202

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cirazoline

METLIN ID

Not Available

PubChem Compound

2765

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Cirazoline (HMDB0250274)

MOL for HMDB0250274 (Cirazoline)

3D MOL for HMDB0250274 (Cirazoline)

3D SDF for HMDB0250274 (Cirazoline)

3D-SDF for HMDB0250274 (Cirazoline)

PDB for HMDB0250274 (Cirazoline)

3D PDB for HMDB0250274 (Cirazoline)

SMILES for HMDB0250274 (Cirazoline)

INCHI for HMDB0250274 (Cirazoline)

Structure for HMDB0250274 (Cirazoline)

3D Structure for HMDB0250274 (Cirazoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra